GB981539A - Manufacture of light stable high molecular polyesters and/or polyamides - Google Patents
Manufacture of light stable high molecular polyesters and/or polyamidesInfo
- Publication number
- GB981539A GB981539A GB23086/62A GB2308662A GB981539A GB 981539 A GB981539 A GB 981539A GB 23086/62 A GB23086/62 A GB 23086/62A GB 2308662 A GB2308662 A GB 2308662A GB 981539 A GB981539 A GB 981539A
- Authority
- GB
- United Kingdom
- Prior art keywords
- benztriazole
- hydroxy
- carboxyethylphenyl
- acid
- carboxylic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title abstract 5
- 229920000728 polyester Polymers 0.000 title abstract 4
- 239000004952 Polyamide Substances 0.000 title abstract 3
- 229920002647 polyamide Polymers 0.000 title abstract 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 abstract 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 6
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 abstract 6
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 abstract 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 abstract 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- UFFRSDWQMJYQNE-UHFFFAOYSA-N 6-azaniumylhexylazanium;hexanedioate Chemical compound [NH3+]CCCCCC[NH3+].[O-]C(=O)CCCCC([O-])=O UFFRSDWQMJYQNE-UHFFFAOYSA-N 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 abstract 2
- 150000001298 alcohols Chemical class 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000000178 monomer Substances 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- SQASHPHWVSAHDM-UHFFFAOYSA-N 4h-benzotriazole-5-carboxylic acid Chemical compound C1C(C(=O)O)=CC=C2N=NN=C21 SQASHPHWVSAHDM-UHFFFAOYSA-N 0.000 abstract 1
- 239000004342 Benzoyl peroxide Substances 0.000 abstract 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract 1
- KZTYYGOKRVBIMI-UHFFFAOYSA-N S-phenyl benzenesulfonothioate Natural products C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 235000011037 adipic acid Nutrition 0.000 abstract 1
- 239000001361 adipic acid Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 1
- -1 benztriazole compound Chemical class 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 150000001721 carbon Chemical group 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 150000001733 carboxylic acid esters Chemical class 0.000 abstract 1
- YWJUZWOHLHBWQY-UHFFFAOYSA-N decanedioic acid;hexane-1,6-diamine Chemical compound NCCCCCCN.OC(=O)CCCCCCCCC(O)=O YWJUZWOHLHBWQY-UHFFFAOYSA-N 0.000 abstract 1
- WMPOZLHMGVKUEJ-UHFFFAOYSA-N decanedioyl dichloride Chemical compound ClC(=O)CCCCCCCCC(Cl)=O WMPOZLHMGVKUEJ-UHFFFAOYSA-N 0.000 abstract 1
- 150000004985 diamines Chemical class 0.000 abstract 1
- 150000001991 dicarboxylic acids Chemical class 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 150000002430 hydrocarbons Chemical group 0.000 abstract 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 150000004702 methyl esters Chemical class 0.000 abstract 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical compound C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
- C08G63/6854—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen derived from polycarboxylic acids and polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
- C08G63/6854—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/6856—Dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/688—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/06—Unsaturated polyesters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
A process for the production of high molecular weight polyesters and polyamides comprises reacting a 2-(21-hydroxyphenyl)benztriazole of the general formula <FORM:0981539/C3/1> where X is a divalent organic bridging member which does not impart colour, Y is a condensable carboxyl group or an aliphatically or cycloaliphatically bound amino or hydroxy group, said amino or hydroxy groups not being bound to an unsaturated carbon atom, or an ester or amide-forming derivative thereof, n is 1 or 2, the nucleus A can contain in the 4-, 5- and 6-positions the grouping -(X-Y) and/or alkyl, alkoxy, carboxy, carboxylic ester or amide, sulphonic acid amide, alkyl sulphonyl or halogens and the nucleus B can contain in the 31-, 41- and 51-positions the grouping -(X-Y) and/or hydrocarbon groups, alkoxy groups or halogens, with polycondensable monomers at temperatures of 150 DEG to 350 DEG C., and, when a carboxylic acid derivative of the benztriazole compound is used in the form of its acid halide at temperatures of 0 DEG to 200 DEG C., benztriazole compounds which contain only reactive hydroxy groups or groups reacting as such only being used for the production of polyesters. The polycondensable monomers are defined as being:-(a) for the production of polyamides: substantially equimolar mixtures of dicarboxylic acid and diamines (or salts thereof) and/or aminocarboxylic acids, and (b) for the production of polyesters: mixtures of dicarboxylic acids (or esters thereof with monohydric alcohols) and dihydric alcohols. The examples describe the preparation of polymers from:-(1) 2 - (21 - hydroxy - 51 - b - carboxyethylphenyl) benztriazole and e -caprolactam; (2) and (3) maleic acid anhydride, phthalic acid anhydride, diethylene glycol, ethylene glycol and 2 - (21 - hydroxy - 51 - b - carboxyethylphenyl) -benztriazole-51-sulphonic acid amide; (4) 1: 1-cyclohexane dicarbinol, dimethyl terephthalate and the methyl ester of 2 - (21 - hydroxy - 51 - b -carboxyethylphenyl)benztriazole - 5 - carboxylic acid; (5) p:p1 - dicarbo - b - hydroxylethyl diphenyl sulphone, adipic acid and 2-(21 -hydroxy-51 - carboxyethylphenyl)benztriazole - 5 -carboxylic acid-b -hydroxyethylamide; (6) ethylene glycol, dimethyl terephthalate and 2-(21 -hydroxy - 31 - o - carboxyphenylmethyl - 51 -methylphenyl) - benztriazole; (7) hexamethylene -diammonium adipate and 2-(21-hydroxy -31 - methyl - 5 - b - carboxyethylphenyl) benztriazole - 5 - carboxylate; (8) hexamethylene diammonium sebacate, hexamethylene diammonium adipate, hexamethylene diamine and 2 - (21 - hydroxy - 51 - b - carboxyethylphenyl)-benztriazole - 5 - carboxylic acid and (9) sebacic acid dichloride, hexamethylene diamine and 2 - (21 - hydroxy - 51 - b - carboxyethylphenyl) -benztriazole - 5 - carboxylic acid. Many other suitable benztriazoles being listed in the examples. The products of Examples (2) and (3) are copolymerized in the presence of benzoyl peroxide with:-(2) styrene and (3) methyl methacrylate. Reference has been directed by the Comptroller to Specification 878,362.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH710361A CH426263A (en) | 1961-06-16 | 1961-06-16 | Process for the production of high molecular weight polyamides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB981539A true GB981539A (en) | 1965-01-27 |
Family
ID=4319999
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB23086/62A Expired GB981539A (en) | 1961-06-16 | 1962-06-15 | Manufacture of light stable high molecular polyesters and/or polyamides |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3862087A (en) |
| AT (1) | AT248698B (en) |
| BE (1) | BE630550A (en) |
| CH (2) | CH426263A (en) |
| DK (2) | DK105002C (en) |
| ES (1) | ES278354A1 (en) |
| FR (1) | FR1325405A (en) |
| GB (1) | GB981539A (en) |
| NL (2) | NL279773A (en) |
| SE (1) | SE312440B (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5112912A (en) * | 1989-03-21 | 1992-05-12 | Ciba-Geigy Corp. | Process for modifying acrylate copolymers |
| US5124723A (en) * | 1989-08-25 | 1992-06-23 | Ciba-Geigy Corporation | Light-stabilized ink composition |
| US5280124A (en) * | 1991-02-12 | 1994-01-18 | Ciba-Geigy Corporation | 5-sulfonyl-substituted benzotriazole UV-absorbers |
| US5298033A (en) * | 1989-03-14 | 1994-03-29 | Ciba-Geigy Corporation | Ultraviolet absorbing lenses and methods of manufacturing thereof |
| US5683861A (en) * | 1996-10-23 | 1997-11-04 | Eastman Kodak Company | Benzotriazole-based UV absorbers and photographic elements containing them |
| US5739348A (en) * | 1996-10-23 | 1998-04-14 | Eastman Kodak Company | Method of synthesizing tert-amido-substituted 2-(2'-hydroxyphenyl) benzotriazole compounds in a one-step process |
| JP2008195961A (en) * | 2008-05-07 | 2008-08-28 | Dainichiseika Color & Chem Mfg Co Ltd | Master batch for functional agent to which polymer is bound, method for manufacturing the same, method for using them, and article using them |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4981914A (en) * | 1987-08-12 | 1991-01-01 | Atochem North America, Inc. | Polymer bound UV stabilizers |
| US5096977A (en) * | 1987-08-12 | 1992-03-17 | Atochem North America, Inc. | Process for preparing polymer bound UV stabilizers |
| US5233047A (en) * | 1987-08-12 | 1993-08-03 | Elf Atochem North America, Inc. | Benzotriazole UV absorber hydrazides |
| US4980420A (en) * | 1987-08-12 | 1990-12-25 | Atochem North America, Inc. | Benzotriazole and oxanilide UV absorber hydrazides |
| US5206378A (en) * | 1987-08-12 | 1993-04-27 | Elf Atochem North America, Inc. | Hydrazido functionalized 2-(2-hydroxyphenyl)-2h-benzotriazoles |
| US4868246A (en) * | 1987-08-12 | 1989-09-19 | Pennwalt Corporation | Polymer bound UV stabilizers |
| KR940002181B1 (en) * | 1990-06-30 | 1994-03-18 | 제일합섬 주식회사 | Elastomer of co-polyester polymer |
| US5393860A (en) * | 1994-02-04 | 1995-02-28 | Hoechst Celanese Corporation | Polymer compositions containing substituted pyrazines |
| DE19513056B4 (en) * | 1995-04-07 | 2005-12-15 | Zimmer Ag | Titanium-containing catalysts and process for the production of polyester |
| JP3448851B2 (en) * | 1997-11-28 | 2003-09-22 | タキロン株式会社 | Additive-containing resin molded article and method for producing the same |
| US8334359B2 (en) | 2008-09-26 | 2012-12-18 | Rhodia Operations | Modified polyamide, method for preparing same, and article obtained from said polyamide |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3213058A (en) * | 1960-12-19 | 1965-10-19 | American Cyanamid Co | Polymers reacted with benzotriazole uv absorbers |
| US3282886A (en) * | 1962-07-27 | 1966-11-01 | Du Pont | Polycarbonamides of improved photostability and dye lightfastness |
-
0
- BE BE630550D patent/BE630550A/xx unknown
- NL NL124488D patent/NL124488C/xx active
- NL NL279773D patent/NL279773A/xx unknown
-
1961
- 1961-06-16 CH CH710361A patent/CH426263A/en unknown
- 1961-06-16 CH CH1275665A patent/CH432842A/en unknown
-
1962
- 1962-06-15 AT AT484562A patent/AT248698B/en active
- 1962-06-15 FR FR900900A patent/FR1325405A/en not_active Expired
- 1962-06-15 DK DK267962AA patent/DK105002C/en active
- 1962-06-15 SE SE6730/62A patent/SE312440B/xx unknown
- 1962-06-15 DK DK347863AA patent/DK103095C/en active
- 1962-06-15 GB GB23086/62A patent/GB981539A/en not_active Expired
- 1962-06-15 ES ES278354A patent/ES278354A1/en not_active Expired
-
1973
- 1973-08-10 US US387310A patent/US3862087A/en not_active Expired - Lifetime
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5298033A (en) * | 1989-03-14 | 1994-03-29 | Ciba-Geigy Corporation | Ultraviolet absorbing lenses and methods of manufacturing thereof |
| US5112912A (en) * | 1989-03-21 | 1992-05-12 | Ciba-Geigy Corp. | Process for modifying acrylate copolymers |
| US5124723A (en) * | 1989-08-25 | 1992-06-23 | Ciba-Geigy Corporation | Light-stabilized ink composition |
| US5280124A (en) * | 1991-02-12 | 1994-01-18 | Ciba-Geigy Corporation | 5-sulfonyl-substituted benzotriazole UV-absorbers |
| US5436349A (en) * | 1991-02-12 | 1995-07-25 | Ciba-Geigy Corporation | Compositions stabilized with 5-sulfonyl-substituted benotriazole UV-absorbers |
| US5683861A (en) * | 1996-10-23 | 1997-11-04 | Eastman Kodak Company | Benzotriazole-based UV absorbers and photographic elements containing them |
| US5739348A (en) * | 1996-10-23 | 1998-04-14 | Eastman Kodak Company | Method of synthesizing tert-amido-substituted 2-(2'-hydroxyphenyl) benzotriazole compounds in a one-step process |
| JP2008195961A (en) * | 2008-05-07 | 2008-08-28 | Dainichiseika Color & Chem Mfg Co Ltd | Master batch for functional agent to which polymer is bound, method for manufacturing the same, method for using them, and article using them |
Also Published As
| Publication number | Publication date |
|---|---|
| US3862087A (en) | 1975-01-21 |
| AT248698B (en) | 1966-08-10 |
| ES278354A1 (en) | 1962-12-01 |
| BE630550A (en) | |
| DK105002C (en) | 1966-08-01 |
| CH426263A (en) | 1966-12-15 |
| FR1325405A (en) | 1963-04-26 |
| DK103095C (en) | 1965-11-15 |
| DE1495870B2 (en) | 1972-12-21 |
| SE312440B (en) | 1969-07-14 |
| NL124488C (en) | |
| DE1495870A1 (en) | 1969-07-31 |
| NL279773A (en) | |
| CH432842A (en) | 1967-03-31 |
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